A chautauqua was a stationary or traveling institution popular in the late nineteenth and early twentieth centuries, providing education usually combined with religious instruction and entertainment in the form of lectures, concerts, or dramatic performances. Guest speakers and entertainment were brought to the Old Salem Chautauqua for a certain period of days each year, usually in August.

The Old Salem Chautauqua Association was founded in Petersburg, Illinois in 1897 as the Old Salem Cumberland Presbyterian State Chautauqua Association. The association held a two-week assembly near New Salem in 1898. By 1909, the gatherings had become popular enough that the association bought fifty-four acres on the Sangamon River a half mile north of the village. The grounds used for the Chautauqua were later plotted and sold to members for cottages and concessions.